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Method for synthesizing Imatinib

A synthetic method, imatinib technology, applied in the field of drug preparation, can solve the problems of unsuitability for industrial production, harsh reaction conditions, expensive raw materials, etc., and achieve the effect of being conducive to industrial production, mild conditions, and low cost

Active Publication Date: 2010-06-16
TIANJIN WEIJIE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for easy manufacturing of certain chemicals called Imatinib through reaction between two different starting materials: Cyanoimides or Intermediate Compounds containing aminopyrimido groups on their molecule structure. These intermediates can then be used either alone or together into other compound structures like this one.

Problems solved by technology

This patented technical problem addressed in this patent relates to improving on existing processes that use costly starting material and require lengthy reactions and severe reaction conditions during manufacturing process.

Method used

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  • Method for synthesizing Imatinib
  • Method for synthesizing Imatinib
  • Method for synthesizing Imatinib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of 4-hydroxymethyl-N-(3-guanidino-4-methylphenyl)benzamide (II)

[0024] Add 0.8g (2.44mmol) 4-hydroxymethyl-N-[4-methyl-3-aminophenyl]benzamide in a 25ml four-necked flask, then add 8ml of n-butanol, heat up to reflux under stirring, Add 0.62g of concentrated hydrochloric acid dropwise, then add 1.8g (21.4mmol) of cyanamide aqueous solution (50% concentration), after reacting overnight, add sodium hydroxide to adjust to alkaline, then filter, remove the solvent in the filtrate, and perform column chromatography , and dried to obtain 0.66 g of light yellow solid. The yield was 70.2%.

[0025] Preparation of 4-hydroxymethyl-N-[4-methyl-3-[[4-(3-pyridine)-2-pyrimidine]amino]phenyl]benzamide (III)

[0026] Add 15ml isopropanol, 0.7g (2.13mmol) 4-hydroxymethyl-N-(3-guanidino-4-methylphenyl) benzamide and 0.38g (2.13mmol) 3 -(3-Dimethylaminoacryl)pyridine, heated to reflux overnight with stirring, then cooled and crystallized to obtain 0.50 g of a bright yello...

Embodiment 2

[0034] Preparation of 4-hydroxymethyl-N-(3-guanidino-4-methylphenyl)benzamide (II)

[0035] Add 4g (15.6mmol) 4-hydroxymethyl-N-[4-methyl-3-aminophenyl]benzamide into a 100ml four-necked flask, then add 25ml of isopropanol, heat up to reflux under stirring, drop Add 3.1g of concentrated hydrochloric acid, then add 6.56g (78.1mmol) of cyanamide aqueous solution (50% concentration), react overnight, add sodium hydroxide to adjust to alkalinity, filter, remove the solvent in the filtrate, add a small amount of water to dissolve After cooling, crystallize slowly, and obtain 3.63 g of light yellow solid after suction filtration and drying. The yield was 78.1%.

[0036] Preparation of 4-hydroxymethyl-N-[4-methyl-3-[[4-(3-pyridine)-2-pyrimidine]amino]phenyl]benzamide (III)

[0037] Add 25ml isoamyl alcohol, 5g (15.3mmol) 4-hydroxymethyl-N-(3-guanidino-4-methylphenyl) benzamide and 3.2g (18.1mmol) 3- (3-Dimethylaminoacryloyl)pyridine was heated to reflux overnight with stirring, th...

Embodiment 3

[0045] Preparation of 4-hydroxymethyl-N-(3-guanidino-4-methylphenyl)benzamide (II)

[0046] Add 10g (30.5mmol) 4-hydroxymethyl-N-[4-methyl-3-aminophenyl]benzamide into a 250ml four-necked flask, then add 62.5ml of ethanol, heat up to reflux under stirring, drop Concentrated hydrochloric acid 7.75g, then add 6.1g (76.2mmol) aqueous solution (50% concentration) of cyanamide, after reacting overnight, add sodium hydroxide to adjust to alkaline, filter, remove the solvent in the filtrate, add a small amount of water to dissolve Slowly crystallize under cooling, and obtain 9.7 g of light yellow solid after suction filtration and drying, with a yield of 80%.

[0047] Preparation of 4-hydroxymethyl-N-[4-methyl-3-[[4-(3-pyridine)-2-pyrimidine]amino]phenyl]benzamide (III)

[0048] Add 45ml isoamyl alcohol, 9g (27.5mmol) 4-hydroxymethyl-N-(3-guanidino-4-methylphenyl) benzamide and 5.76g (32.7mmol) 3- (3-Dimethylaminoacryloyl)pyridine was heated to reflux under stirring, a small amount...

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Abstract

The invention discloses a method for synthesizing Imatinib. In the method, 4-methylol-N-[4-methyl-3-aminophenyl] benzamide is used as the raw material to carry out addition reaction with cyanamide to obtain an intermediate 4-methylol-N-(3-guanidyl-4-methylphenyl) benzamide (II), the intermediate (II) carries out condensation reaction with 3-(3-dimethylamino allyl acyl) pyridine to obtain an intermediate 4-methylol-N-[4-methyl-3-[[4-(3-pyridine)-2-pyrimidine] amino] phenyl] benzamide (III), the intermediate (III) reacts with substituted benzene sulfonyl chloride to obtain an intermediate 4-[ substituted benzenesulfonic acid carbomethoxy]-N-[4-methyl-3-[[4-(3-pyridine)-2-pyrimidine] amino] phenyl] benzamide (IV), and finally the intermediate (IV) reacts with methylpiperazine to obtain the Imatinib (V). The method has simple route process, mild conditions, high product purity and yield, and comparatively low cost and is beneficial to industrialized production.

Description

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Claims

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Application Information

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Owner TIANJIN WEIJIE TECH
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